N-[(S)-1-phenylethyl]-N-[(S)-1-(2,4,10-trioxaadamant-3-yl)propyl]amine | 1392441-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(S)-1-phenylethyl]-N-[(S)-1-(2,4,10-trioxaadamant-3-yl)propyl]amine
• 英文别名: (1S)-N-[(1S)-1-phenylethyl]-1-(2,4,10-trioxatricyclo[3.3.1.13,7]decan-3-yl)propan-1-amine
• CAS: 1392441-56-3
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: FQBXTEGJOPFXHU-HZMQBGIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(S)-1-phenylethyl]-N-[(S)-1-(2,4,10-trioxaadamant-3-yl)propyl]amine 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、405.33 kPa 条件下， 反应 16.0h， 以96%的产率得到(S)-1-(2,4,10-trioxaadamant-3-yl)propylamine
  参考文献：
  名称：

  An approach to chiral amino acids via reductive amination of ketones: hydride reduction of 1-(S)-phenethyl amine derived Schiff bases of C-protected α-keto acids

  摘要：

  Various 1-acyl-2,4,10-trioxaadamantanes were prepared from the corresponding 1-methoxycarbonyl derivatives, via conversion to the N-acylpiperidine derivatives followed by reaction with a Grignard reagent in refluxing THF. These alpha-keto orthoformates were converted to the corresponding imines with 1-(S)-phenethyl amine (TiCl4/Et3N/toluene/reflux), with the Schiff bases being reduced further with NaBH4 (MeOH/0 degrees C) into the corresponding 1-(S)-phenethyl amines (diastereomeric excess 91:9 by NMR). Hydrogenolysis of the phenethyl group (Pd-C/MeOH) finally led to the 1-(aminoalkyl)trioxaadamantanes, which are chiral C-protected alpha-amino acids, in excellent overall yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.017
• 作为产物：
  描述：

  piperidin-1-yl(2,4,10-trioxatricyclo[3.3.1.13,7]decan-3-yl)methanone 在 甲醇 、 sodium tetrahydroborate 、 碘 、 四氯化钛 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.75h， 生成 N-[(S)-1-phenylethyl]-N-[(S)-1-(2,4,10-trioxaadamant-3-yl)propyl]amine 、 N-[(S)-1-phenylethyl]-N-[(R)-1-(2,4,10-trioxaadamant-3-yl)propyl]amine
  参考文献：
  名称：

  An approach to chiral amino acids via reductive amination of ketones: hydride reduction of 1-(S)-phenethyl amine derived Schiff bases of C-protected α-keto acids

  摘要：

  Various 1-acyl-2,4,10-trioxaadamantanes were prepared from the corresponding 1-methoxycarbonyl derivatives, via conversion to the N-acylpiperidine derivatives followed by reaction with a Grignard reagent in refluxing THF. These alpha-keto orthoformates were converted to the corresponding imines with 1-(S)-phenethyl amine (TiCl4/Et3N/toluene/reflux), with the Schiff bases being reduced further with NaBH4 (MeOH/0 degrees C) into the corresponding 1-(S)-phenethyl amines (diastereomeric excess 91:9 by NMR). Hydrogenolysis of the phenethyl group (Pd-C/MeOH) finally led to the 1-(aminoalkyl)trioxaadamantanes, which are chiral C-protected alpha-amino acids, in excellent overall yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.017

文献信息

• An approach to chiral amino acids via reductive amination of ketones: hydride reduction of 1-(S)-phenethyl amine derived Schiff bases of C-protected α-keto acids
  作者：Sosale Chandrasekhar、V. Mohana Rao

  DOI：10.1016/j.tetasy.2012.06.017

  日期：2012.7

  Various 1-acyl-2,4,10-trioxaadamantanes were prepared from the corresponding 1-methoxycarbonyl derivatives, via conversion to the N-acylpiperidine derivatives followed by reaction with a Grignard reagent in refluxing THF. These alpha-keto orthoformates were converted to the corresponding imines with 1-(S)-phenethyl amine (TiCl4/Et3N/toluene/reflux), with the Schiff bases being reduced further with NaBH4 (MeOH/0 degrees C) into the corresponding 1-(S)-phenethyl amines (diastereomeric excess 91:9 by NMR). Hydrogenolysis of the phenethyl group (Pd-C/MeOH) finally led to the 1-(aminoalkyl)trioxaadamantanes, which are chiral C-protected alpha-amino acids, in excellent overall yields. (C) 2012 Elsevier Ltd. All rights reserved.